US6541473B2ExpiredUtilityPatentIndex 57
Resorcinol derivatives
Est. expirySep 21, 2020(expired)· nominal 20-yr term from priority
Inventors:BRADLEY STUART ECOLLINGTON ERIC WFYFE MATTHEW CGATTRELL WILLIAM TGEDEN JOANNA VMURRAY PETER JPROCTER MARTIN JROWLEY ROBERT JWILLIAMS JONATHAN G
A61P 29/00C07C 2601/14C07D 487/04C07C 275/28C07D 231/16A61K 8/492C07C 259/10A61K 8/4973C07C 59/54A61K 8/70A61K 8/42A61P 17/06C07D 307/24C07C 69/732C07D 333/38C07D 207/267C07D 207/16C07C 271/66C07D 307/94C07C 233/23C07C 233/58A61P 17/00A61Q 19/02C07D 213/81A61K 8/4986C07C 2601/16A61P 17/02C07D 213/82C07C 233/74C07D 237/04C07C 271/24C07C 235/36C07D 209/24C07D 231/14C07C 69/96C07D 339/06C07D 307/79A61K 8/35A61K 8/4946A61K 8/69A61K 8/4926C07C 311/49C07C 255/57C07D 209/42C07D 317/72C07D 213/56C07D 235/24C07C 271/56C07D 303/14C07C 255/36
57
PatentIndex Score
2
Cited by
3
References
29
Claims
Abstract
The present invention relates to certain resorcinol derivatives and their use as skin lightening agents.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein:
R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3 wherein R 1 and R 2 are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 - 6 )alkyl, and R 3 is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5 wherein R 4 is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5 is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —O-aryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkyl heteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenylaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthalenyl, wherein X is O, S, SO, SO 2 or NR 1 ; —N(R 1 )OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6 wherein R 6 is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7 wherein R 7 is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C 6 )alkyl, —CO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8 wherein R 8 is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;
with the proviso that the cycloalkenyl ring is not aromatic.
2. A compound of claim 1 , wherein R is substituted by —N(R 1 )CONR 2 R 3 .
3. A compound of claim 1 , wherein R is substituted by —N(R 4 )COR 5 .
4. A compound of claim 1 , wherein R is substituted by —N(R 1 )OCOaryl.
5. A compound of claim 1 , wherein R is substituted by ═CHCO 2 R 1 .
6. A compound of claim 1 , wherein R is substituted by ═CHCONR 1 R 2 .
7. A compound of claim 1 , wherein R is substituted by ═CHCN.
8. A compound of claim 1 , wherein R is substituted by ═NNHSO 2 R 6 .
9. A compound of claim 1 , wherein R is substituted by —N(O)═CHR 6 .
10. A compound of claim 1 , wherein R is substituted by —OC(O)NR 1 R 7 .
11. A compound of claim 1 , wherein R is substituted by amino(C 1 -C 6 )alkylarylCO 2 —.
12. A compound of claim 1 , wherein R is substituted by —OC(O)OR 8 .
13. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by ═CH 2 ; with the proviso that the cycloalkenyl ring is not aromatic.
14. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein R is 3-cyclohexenyl.
15. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring, wherein one of the carbon atoms of said cycloalkyl or cycloalkenyl ring is substituted by two groups such that the said groups are taken together with the carbon to which they are attached to form a ring of the formula:
wherein X is O, S, SO, SO 2 or NR 1 , wherein R 1 is as defined above; Z is CH 2 , O, S, SO or SO 2 ; m is 0-3; with the proviso that when m=0, then Z is CH 2 ; and with the proviso that the cycloalkenyl ring is not aromatic.
16. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring, wherein one of the carbon atoms of said cycloalkyl or cycloalkenyl ring is substituted by two groups such that the said groups are taken together with the carbon to which they are attached to form a ring of the formula:
wherein X is O, S, SO, SO 2 or NR 1 , wherein R 1 is as defined above; and m is 0-3; and with the proviso that the cycloalkenyl ring is not aromatic.
17. A compound selected from the group consisting of:
4-(1,4-Dioxaspiro[4.5]dec-8-yl)1,3-benzenediol;
(±)-{4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid;
(±)-[4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrile;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]benzamide;
trans-4-{4-[(Z)-benzyl idene(oxido)amino]cyclohexyl}-1,3-benzenediol;
trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
syn-8-(2,4-Dihydroxyphenyl)-1-oxaspiro[4.5]decan-2-one;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N′-phenylurea;
trans-Phenyl-4-(2,4-dihydroxyphenyl)cyclohexylcarbamate;
cis-N-Benzyl-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N′-ethylurea;
cis-N-Benzyl-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]propanamide;
trans-4-(2,4-Dihydroxyphenyl)cyclohexylphenylcarbamate;
trans-Ethyl[({[4-(2,4-dihydroxyphenyl)cyclohexyl]oxy}carbonyl)amino]acetate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl benzylcarbamate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl ethyl carbonate;
trans-Methyl[({[4-(2,4-dihydroxyphenyl)cyclohexyl]oxy}carbonyl)amino]acetate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl methyl imidodicarbonate;
cis/trans-4-(1-Oxaspiro[2.5]oct-6-yl)-1,3-benzenediol;
4-(4-Methylenecyclohexyl)-1,3-benzenediol;
4-(3-Cyclohexen-1-yl)-1,3-benzenediol;
trans4-(2,4-Dihydroxyphenyl)cyclohexyl(2R)-2-amino-3-phenylpropanoate;
Benzyl [4-(2,4-dihydroxyphenyl)cyclohexylidene]acetate;
4-(1,4-Dithiaspiro[4.5]dec-8-yl)-1,3-benzenediol;
N′-[4-(2,4-Dihydroxyphenyl)cyclohexylidene]4-methylbenzenesulfonohydrazide;
trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-3-nitrobenzamide;
trans-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N′-phenylurea;
trans-N-[4-(dihydroxyphenyl)cyclohexyl]-2,2,2-trifluoroacetamide;
cis-3-cyano-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
cis-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxy-4-(trifluoromethyl)benzamide;
cis-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxy-4-methoxybenzamide;
(±)-Methyl[4-(2,4-dihydroxyphenyl)cyclohexylidene]acetate;
and a pharmaceutically acceptable salt thereof.
18. A pharmaceutical composition for lightening skin or reducing the pigmentation of skin in a human, comprising a pharmaceutically acceptable carrier, and a skin-lightening or pigmentation-reducing amount of a compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein:
R is a (C 3 -C 8 )cycloalkyl or (C 1 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3 wherein R 1 and R 2 are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3 is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5 wherein R 4 is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5 is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —O-aryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkyl heteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -C 7 )alkenylaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthalenyl, wherein X is O, S, SO, SO 2 or NR 1 ; —N(R 1 )OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6 wherein R 6 is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7 wherein R 7 is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C 6 )alkyl, —CO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8 wherein R 8 is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl;
with the proviso that the cycloalkenyl ring is not aromatic.
19. A pharmaceutical composition for lightening skin or reducing the pigmentation of skin in a human, comprising a pharmaceutically acceptable carrier, and a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by ═CH 2 ; with the proviso that the cycloalkenyl ring is not aromatic.
20. A pharmaceutical composition for lightening skin or reducing the pigmentation of skin in a human, comprising a pharmaceutically acceptable carrier, and a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is 3-cyclohexenyl.
21. A pharmaceutical composition for lightening skin or reducing the pigmentation of skin in a human, comprising a pharmaceutically acceptable carrier, and a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring, wherein one of the carbon atoms of said cycloalkyl or cycloalkenyl ring is substituted by two groups such that the said groups are taken together with the carbon to which they are attached to form a ring of the formula:
wherein X is O, S, SO, SO 2 or NR 1 , wherein R 1 is as defined above; Z is CH 2 , O, S, SO or SO 2 ; m is 0-3; with the proviso that when m=0, then Z is CH 2 ; and with the proviso that the cycloalkenyl ring is not aromatic.
22. A pharmaceutical composition for lightening skin or reducing the pigmentation skin in a human, comprising a pharmaceutically acceptable carrier, and a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring, wherein one of the carbon atoms of said cycloalkyl or cycloalkenyl ring is substituted by two groups such that the said groups are taken together with the carbon to which they are attached to form a ring of the formula:
wherein X is O, S, SO, SO 2 or NR 1 , wherein R 1 is as defined above; and m is 0-3; and with the proviso that the cycloalkenyl ring is not aromatic.
23. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a skin-lightening or pigmentation-reducing effective amount of a compound selected from the group consisting of:
4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol;
(±)-{4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid;
(±)-[4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrile;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]benzamide;
trans-4-{4-[(Z)-benzylidene(oxido)amino]cyclohexyl}-1,3-benzenediol;
trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
syn-8-(2,4-Dihydroxyphenyl)-1-oxaspiro[4.5]decan-2-one;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N′-phenylurea;
trans-Phenyl-4-(2,4-dihydroxyphenyl)cyclohexylcarbamate;
cis-N-Benzyl-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N′-ethylurea;
cis-N-Benzyl-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]propanamide;
trans-4-(2,4-Dihydroxyphenyl)cyclohexylphenylcarbamate;
trans-Ethyl[({[4-(2,4-dihydroxyphenyl)cyclohexyl]oxy}carbonyl)amino]acetate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl benzylcarbamate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl ethyl carbonate;
trans-Methyl[({[4-(2,4-dihydroxyphenyl)cyclohexyl]oxy}carbonyl)amino]acetate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl methyl imidodicarbonate;
cis/trans-4-(1-Oxaspiro[2.5]oct-6-yl)-1,3-benzenediol;
4-(4-Methylenecyclohexyl)-1,3-benzenediol;
4-(3-Cyclohexen-1-yl)-1,3-benzenediol;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl (2R)-2-amino-3-phenylpropanoate;
Benzyl[4-(2,4-dihydroxyphenyl)cyclohexylidene]acetate;
4-(1,4-Dithiaspiro[4.5]dec-8-yl)-1,3-benzenediol;
N′-[4-(2,4-Dihydroxyphenyl)cyclohexylidene]-4-methylbenzenesulfanohydrazide;
trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-3-nitrobenzamide;
trans-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N′-phenylurea;
trans-N-[4-(dihydroxyphenyl)cyclohexyl]-2,2,2-trifluoroacetamide;
cis-3-cyano-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
cis-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxy-4-(trifluoromethyl)benzamide;
cis-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxy-4-methoxybenzamide;
(±)-Methyl[4-(2,4-dihydroxyphenyl)cyclohexylidene]acetate;
and a pharmaceutically acceptable salt thereof.
24. A method of lightening skin in a human, comprising administering to said human a skin-lightening or pigmentation-reducing effective amount of a compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein:
R is a (C 3 -C 8 )cycloalkyl or (C 1 -C 8 )cycloalkenyl ring substituted by —N(R 1 )CONR 2 R 3 wherein R 1 and R 2 are independently selected from hydrogen, (C 1 -C 6 )alkyl, and aryl(C 1 -C 6 )alkyl, and R 3 is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl; —N(R 4 )COR 5 wherein R 4 is hydrogen, (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl-, or OH and R 5 is (C 7 -C 10 )alkyl, aryl, aryl(C 1 -C 6 )alkyl-, —O-aryl, CF 3 , heterocycloalkyl, —(C 1 -C 6 )alkylheterocycloalkyl, —(C 2 -C 7 )alkenylheterocycloalkyl, heteroaryl, —(C 1 -C 6 )alkyl heteroaryl, —(C 2 -C 7 )alkenylheteroaryl, —(C 2 -Cl)alkenylaryl, —(C 2 -C 7 )alkenylCOaryl, —(C 1 -C 6 )alkylN(R 4 )CO-aryl, —(C 1 -C 6 )alkylCO-aryl, —(C 1 -C 6 )alkylhydroxyaryl, —(C 1 -C 6 )alkyl-X-aryl, (C 2 -C 7 )alkenyl, benzyhydryl, 5-hydroxyoxoindanyl, or tetrahydronaphthalenyl, wherein X is O, S, SO, SO 2 or NR 1 ; —N(R 1 )OCOaryl; ═CHCO 2 R 1 ; ═CHCONR 1 R 2 ; ═CHCN; ═NNHSO 2 R 6 wherein R 6 is aryl; —N(O)═CHR 6 ; —OC(O)NR 1 R 7 wherein R 7 is aryl, aryl(C 1 -C 6 )alkyl-, —(C 1 -C 6 )alkylCO 2 (C 1 -C 6 )alkyl, —CO 2 (C 1 -C6)alkyl, —CO 2 aryl, or —CO 2 (C 1 -C 6 )alkylaryl; amino(C 1 -C 6 )alkylarylCO 2 —; or —OC(O)OR 8 wherein R 8 is (C 1 -C 6 )alkyl, aryl(C 1 -C 6 )alkyl, or aryl; with the proviso that the cycloalkenyl ring is not aromatic.
25. A method of lightening skin in a human, comprising administering to said human a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring substituted by ═CH 2 ; with the proviso that the cycloalkenyl ring is not aromatic.
26. A method of lightening skin in a human, comprising administering to said human a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is 3-cyclohexenyl.
27. A method of lightening skin in a human, comprising administering to said human a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring, wherein one of the carbon atoms of said cycloalkyl or cycloalkenyl rings is substituted by two groups such that the said groups are taken together with the carbon to which they are attached to form a ring of the formula:
wherein X is O, S, SO, SO 2 or NR 1 , wherein R 1 is as defined above; Z is CH 2 , O, S, SO or SO 2 ; m is 0-3; with the proviso that when m O, then Z is CH 2 ; and with the proviso that the cycloalkenyl ring is not aromatic.
28. A method of lightening skin in a human, comprising administering to said human a skin-lightening or pigmentation-reducing effective amount of a compound of formula I,
or a pharmaceutically acceptable salt thereof, wherein R is a (C 3 -C 8 )cycloalkyl or (C 5 -C 8 )cycloalkenyl ring, wherein one of the carbon atoms of said cycloalkyl or cycloalkenyl rings is substituted by two groups such that the said groups are taken together with the carbon to which they are attached to form a ring of the formula:
wherein X is O, S, SO, SO 2 or NR 1 , wherein R 1 is as defined above; and m is 0-3; and with the proviso that the cycloalkenyl ring is not aromatic.
29. A method of lightening skin in a human, comprising administering to said human a skin-lightening or pigmentation-reducing effective amount of a compound selected from the group consisting of:
4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol;
(±)-{4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid;
(±)-[4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrile;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]benzamide;
trans-4-{4-[(Z)-benzylidene(oxido)amino]cyclohexyl}-1,3-benzenediol;
trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
syn-8-(2,4-Dihydroxyphenyl)-1-oxaspiro[4.5]decan-2-one;
cis-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-N′-phenylurea;
trans-Phenyl-4-(2,4-Dihydroxyphenyl)cyclohexylcarbamate;
cis-N-Benzyl-N-[4-(2,4dihydroxyphenyl)cyclohexyl]-N′-ethylurea;
cis-N-Benzyl-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]propanamide;
trans-4-(2,4-Dihydroxyphenyl)cyclohexylphenylcarbamate;
trans-Ethyl[({[4-(2,4-dihydroxyphenyl)cyclohexyl]oxy}carbonyl)amino]acetate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl benzylcarbamate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl ethyl carbonate;
trans-Methyl[({[4-(2,4-dihydroxyphenyl)cyclohexyl]oxy}carbonyl)amino]acetate;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl methyl imidodicarbonate;
cis/trans-4-(1-Oxaspiro[2.5]oct-6-yl)-1,3-benzenediol;
4-(4-Methylenecyclohexyl)-1,3-benzenediol;
4-(3-Cyclohexen-1-yl)-1,3-benzenediol;
trans-4-(2,4-Dihydroxyphenyl)cyclohexyl (2R)-2-amino-3-phenylpropanoate;
Benzyl[4-(2,4-dihydroxyphenyl)cyclohexylidene]acetate;
4-(1,4-Dithiaspiro[4.5]dec-8-yl)-1,3-benzenediol;
N′-[4-(2,4-Dihydroxyphenyl)cyclohexylidene]-4-methylbenzenesulfonohydrazide;
trans-N-[4-(2,4-Dihydroxyphenyl)cyclohexyl]-3-nitrobenzamide;
trans-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N′-phenylurea;
trans-N-[4-(dihydroxyphenyl)cyclohexyl]-2,2,2-trifluoroacetamide;
cis-3-cyano-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxybenzamide;
cis-N-[4-(2,4dihydroxyphenyl)cyclohexyl]-N-hydroxy4-(trifluoromethyl)benzamide;
cis-N-[4-(2,4-dihydroxyphenyl)cyclohexyl]-N-hydroxy-4-methoxybenzamide;
(±)-Methyl[4-(2,4-dihydroxyphenyl)cyclohexylidene]acetate;
and a pharmaceutically acceptable salt thereof.Cited by (0)
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